(+)-(1R,4S,5S)-2-(4-tert-butylphenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene

Base Information

• Chemical Name: (+)-(1R,4S,5S)-2-(4-tert-butylphenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene
• CAS No.: 1086432-07-6
• Molecular Formula: C₂₁H₂₈O
• Molecular Weight: 296.453
• Mol file: 1086432-07-6.mol

Synonyms:(+)-(1R,4S,5S)-2-(4-tert-butylphenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene

Chemical Property of (+)-(1R,4S,5S)-2-(4-tert-butylphenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1R,4S,5S)-2-(4-tert-butylphenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene

There total 4 articles about (+)-(1R,4S,5S)-2-(4-tert-butylphenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 43.0%

(-)-(1R,4S,8S)-8-methoxy-1,8-dimethylbicyclo[2.2.2]octa-2,5-dien-2-yltrifluoromethanesulfonate (1086431-99-3) + p-tert-butylphenylboronic acid (123324-71-0) → (+)-(1R,4S,5S)-2-(4-tert-butylphenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene (1086432-07-6)

Guidance literature:

With 1,1'-bis(diphenylphosphino)ferrocene; palladium diacetate; potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.200803230

Reference yield:

5-(1-(bromomethyl)-1-methoxyethyl)-2-methylcyclohex-2-enone (127400-19-5,127400-27-5) → (+)-(1R,4S,5S)-2-(4-tert-butylphenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene (1086432-07-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium tert-butylate / tert-butyl alcohol; tetrahydrofuran / 8 h / 20 °C / Sealed tube; Inert atmosphere

2.1: lithium diisopropyl amide / 1 h / -78 °C / Sealed tube; Inert atmosphere

2.2: -78 - 20 °C

3.1: palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene; potassium carbonate / N,N-dimethyl-formamide / 1 h / 100 °C / Sealed tube; Inert atmosphere

With 1,1'-bis-(diphenylphosphino)ferrocene; potassium tert-butylate; palladium diacetate; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1002/anie.202105800

Reference yield:

C11H16O2 (128657-12-5,671211-41-9) → (+)-(1R,4S,5S)-2-(4-tert-butylphenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene (1086432-07-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / 1 h / -78 °C / Sealed tube; Inert atmosphere

1.2: -78 - 20 °C

2.1: palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene; potassium carbonate / N,N-dimethyl-formamide / 1 h / 100 °C / Sealed tube; Inert atmosphere

With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; potassium carbonate; lithium diisopropyl amide; In N,N-dimethyl-formamide;

DOI:10.1002/anie.202105800

upstream raw materials:

(-)-(1R,4S,8S)-8-methoxy-1,8-dimethylbicyclo[2.2.2]octa-2,5-dien-2-yltrifluoromethanesulfonate

p-tert-butylphenylboronic acid

(S)-p-mentha-6,8-dien-2-one

5-(1-(bromomethyl)-1-methoxyethyl)-2-methylcyclohex-2-enone